What is the cheapest airline that flies from Chicago Midway to Milan?

KLM and Delta are the most popular carriers operating from Chicago Midway to Milan

When did momondo last update prices for flights from Chicago Midway Airport to Milan?

Prices for flights from Chicago Midway Airport to Milan are updated daily.

How old do you have to be to fly from Chicago Midway Airport to Milan?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.

What documentation or ID do you need to fly to Milan?

The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$233 Cheap Flights from Chicago Midway Airport to Milan in 2025/26

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago Midway Airport to Milan

Round-trip

One-way

Last minute

Cheap round-trip flights

1:05 pm - 9:05 amMDW-MXP

13h 00m1 stop

11:05 am - 11:32 pmMXP-MDW

19h 27m1 stop

$823KLM

Find Deal

Sun, Nov 9 - Tue, Nov 25

1:05 pm - 9:05 amMDW-MXP

13h 00m1 stop

10:05 am - 9:46 pmMXP-MDW

17h 41m1 stop

$830Delta

Find Deal

Sun, Mar 1 - Thu, Mar 12

1:14 pm - 9:45 amMDW-MXP

13h 31m2 stops

12:00 pm - 11:32 pmMXP-MDW

18h 32m2 stops

$834Delta

Find Deal

Sun, Nov 9 - Tue, Nov 25

6:00 am - 9:05 amMDW-MXP

20h 05m1 stop

11:05 am - 12:01 pmMXP-MDW

31h 56m1 stop

$836Delta

Find Deal

Sun, Feb 15 - Wed, Feb 25

4:30 pm - 9:05 amMDW-MXP

33h 35m1 stop

9:25 am - 9:56 amMXP-MDW

31h 31m2 stops

$841Delta

Find Deal

Sat, Feb 14 - Tue, Feb 24

4:30 pm - 9:05 amMDW-MXP

33h 35m1 stop

11:05 am - 9:56 amMXP-MDW

29h 51m1 stop

$843Delta

Find Deal

Sat, Feb 14 - Tue, Feb 24

1:05 pm - 9:05 amMDW-MXP

13h 00m1 stop

11:00 am - 6:34 pmMXP-MDW

37h 34m2 stops

$846Delta

Find Deal

Sun, Mar 1 - Fri, Mar 13

4:30 pm - 9:05 amMDW-MXP

33h 35m1 stop

11:00 am - 12:01 pmMXP-MDW

31h 01m2 stops

$847Delta

Find Deal

Sat, Feb 28 - Fri, Mar 13

5:00 am - 8:05 amMDW-MXP

20h 05m1 stop

11:05 am - 11:32 pmMXP-MDW

19h 27m1 stop

$864

Find Deal

Sun, Nov 2 - Tue, Nov 18

5:00 am - 8:05 amMDW-MXP

20h 05m1 stop

12:00 pm - 11:32 pmMXP-MDW

18h 32m2 stops

$868KLM

Find Deal

Sun, Nov 2 - Tue, Nov 18

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets

Delta

Mar 1

MDW1:05 pmChicago Midway

13h 00m

1 stop

MXP9:05 amMilan Malpensa

Mar 12

MXP10:05 amMilan Malpensa

17h 41m

1 stop

MDW9:46 pmChicago Midway

$830

Find similar

Delta

Nov 9

MDW1:14 pmChicago Midway

13h 31m

2 stops

MXP9:45 amMilan Malpensa

Nov 25

MXP12:00 pmMilan Malpensa

18h 32m

2 stops

MDW11:32 pmChicago Midway

$834

Find similar

Delta

Feb 15

MDW6:00 amChicago Midway

20h 05m

1 stop

MXP9:05 amMilan Malpensa

Feb 25

MXP11:05 amMilan Malpensa

31h 56m

1 stop

MDW12:01 pmChicago Midway

$836

Find similar

KLM flights from Chicago Midway Airport to Milan

Our best KLM deals on Chicago Midway Airport to Milan flight tickets

KLM

Nov 9

MDW1:05 pmChicago Midway

13h 00m

1 stop

MXP9:05 amMilan Malpensa

Nov 25

MXP11:05 amMilan Malpensa

19h 27m

1 stop

MDW11:32 pmChicago Midway

$823

Find similar

KLM

Nov 2

MDW5:00 amChicago Midway

20h 05m

1 stop

MXP8:05 amMilan Malpensa

Nov 18

MXP12:00 pmMilan Malpensa

18h 32m

2 stops

MDW11:32 pmChicago Midway

$868

Find similar

KLM

Nov 12

MDW1:05 pmChicago Midway

13h 00m

1 stop

MXP9:05 amMilan Malpensa

Feb 24

MXP11:05 amMilan Malpensa

17h 41m

1 stop

MDW9:46 pmChicago Midway

$905

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 11/9

1:05 pm-9:05 am

1 stop13h 00m

Milan Malpensa

Tue 11/25

11:05 am-11:32 pm

1 stop19h 27m

$823

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 3/1

1:05 pm-9:05 am

1 stop13h 00m

Milan Malpensa

Thu 3/12

10:05 am-9:46 pm

1 stop17h 41m

$830

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 11/9

1:14 pm-9:45 am

2 stops13h 31m

Milan Malpensa

Tue 11/25

12:00 pm-11:32 pm

2 stops18h 32m

$834

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 2/15

6:00 am-9:05 am

1 stop20h 05m

Milan Malpensa

Wed 2/25

11:05 am-12:01 pm

1 stop31h 56m

$836

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 2/14

4:30 pm-9:05 am

1 stop33h 35m

Milan Malpensa

Tue 2/24

9:25 am-9:56 am

2 stops31h 31m

$841

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 2/14

4:30 pm-9:05 am

1 stop33h 35m

Milan Malpensa

Tue 2/24

11:05 am-9:56 am

1 stop29h 51m

$843

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 3/1

1:05 pm-9:05 am

1 stop13h 00m

Milan Malpensa

Fri 3/13

11:00 am-6:34 pm

2 stops37h 34m

$846

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sat 2/28

4:30 pm-9:05 am

1 stop33h 35m

Milan Malpensa

Fri 3/13

11:00 am-12:01 pm

2 stops31h 01m

$847

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 11/2

5:00 am-8:05 am

1 stop20h 05m

Milan Malpensa

Tue 11/18

11:05 am-11:32 pm

1 stop19h 27m

$864

ChicagoMilan

MDW - MXP

MDWMXP

Chicago Midway

Sun 11/2

5:00 am-8:05 am

1 stop20h 05m

Milan Malpensa

Tue 11/18

12:00 pm-11:32 pm

2 stops18h 32m

$868

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,179. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,498.

What is the cheapest time of day to depart on your flight to Milan?

In the morning is the cheapest time of day to fly from Chicago Midway Airport to Milan when you can find flight prices for as low as $703. Flying to Milan in the morning is an ideal time because this is during off-peak travel hours. Flights to Milan are more costly in the evening, with an average ticket price of $1,345. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

When to book flights from Chicago Midway Airport to Milan

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Milan according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Direct flights	None

There are no direct flights from Chicago Midway Airport to Milan. There are no popular flight routes from Chicago Midway Airport to Milan.

Search flight deals

How far is Chicago Midway to Milan by plane?
Milan is 4534.8 mi away from Chicago Midway. Flights usually cover this in 12h 32m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago Midway Airport to Milan?
Prices for flights from Chicago Midway Airport to Milan are updated daily.
How old do you have to be to fly from Chicago Midway Airport to Milan?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Milan.
What documentation or ID do you need to fly to Milan?
The necessary travel and health documents for your Milan trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Bellagio

Varenna

Menaggio

Livigno

Brescia

Stresa

Assago

Monza

Rho

Levanto

Domodossola

Bormio

Crema

Bellano

Lecco

Cernobbio

Novara

Moltrasio

Saronno

Lainate

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Finding the right flight to Milan from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Milan quick and easy, saving you time and money.

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Milan from Chicago with this policy.

How can momondo help me find flights from Chicago to Milan?

Once you have performed a search for Chicago to Milan flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Milan now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Milan and let you know when they change.

An easier way to manage your Milan trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Wed 10/15

Wed 10/22

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Italy

Fly into one of these airports located in Milan

Milan Linate Airport

Milan Malpensa Airport

Cheap flights from Chicago Midway Airport to Milan from $233

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Milan departing on 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago Midway Airport to Milan

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Delta flights from Chicago Midway Airport to Milan

Our best Delta deals on Chicago Midway Airport to Milan flight tickets

KLM flights from Chicago Midway Airport to Milan

Our best KLM deals on Chicago Midway Airport to Milan flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Milan that are best for you.

See travel insights to Milan from

How to get the cheapest flight ticket from Chicago Midway Airport to Milan

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Milan?

Our data shows that Tuesday is the least expensive day to fly to Milan. Tickets to fly out on this day can be as low as $1,179. The most expensive day to fly to Milan is Saturday, with ticket prices averaging around $1,498.

What is the cheapest time of day to depart on your flight to Milan?

What is the cheapest airline that flies from Chicago Midway to Milan?

KLM and Delta are the most popular carriers operating from Chicago Midway to Milan

When to book flights from Chicago Midway Airport to Milan

Cheap Chicago Midway Airport to Milan (MDW to MIL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Milan

Direct flights

How far is Chicago Midway to Milan by plane?

When did momondo last update prices for flights from Chicago Midway Airport to Milan?

How old do you have to be to fly from Chicago Midway Airport to Milan?

What documentation or ID do you need to fly to Milan?

Traveling to a place near Milan?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Milan?

Can I find flights from Chicago to Milan with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Milan?

I’m not ready to book a flight from Chicago to Milan right now. Can momondo alert me if prices change?

An easier way to manage your Milan trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Italy

Fly into one of these airports located in Milan

Airports listed have a maximum distance of 25.0 mi from Milan